Asymmetric synthesis of 3,3′-pyrrolidinyl-dispirooxindoles via a one-pot organocatalytic Mannich/deprotection/aza-Michael sequence

被引：81

作者：

Zhao, Kun ^{[1
]}

Zhi, Ying ^{[1
]}

Li, Xinyi ^{[1
]}

Puttreddy, Rakesh ^{[2
]}

Rissanen, Kari ^{[2
]}

Enders, Dieter ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, Landoltweg 1, D-52074 Aachen, Germany

[2] Univ Jyvaskyla, Dept Chem, Nanosci Ctr, FI-40014 Jyvaskyla, Finland

来源：

CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 11期

基金：

欧洲研究理事会;

关键词：

HIGHLY ENANTIOSELECTIVE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; SPIROCYCLIC OXINDOLES; CONSTRUCTION; CASCADE; STEREOCENTERS; SPIROOXINDOLES; DERIVATIVES; CATALYSIS;

D O I：

10.1039/c5cc10057g

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly stereoselective synthesis of functionalized 3,3'-pyrrolidinyl-dispirooxindole derivatives with three stereogenic centers, including two contiguous spiro-stereocenters, has been achieved through an organocatalytic Mannich/Boc-deprotection/aza-Michael sequence. Employing the commercially available (DHQD)(2)PHAL as the catalyst, the scalable reaction occurs with good yields and excellent stereo-selectivities, providing a short entry into a series of 3,3'-pyrrolidinyl-dispirooxindoles of potentially medical value.

引用

页码：2249 / 2252

页数：4

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